Organic Chemistry
Organic Chemistry
6th Edition
ISBN: 9781936221349
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
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Chapter 28, Problem 28.22P
Interpretation Introduction

(a)

Interpretation:

The curved-arrow mechanism for the anionic oxyCope reaction of compound A is to be given and the stereoisomer B does not react under the same conditions-the statement is to be explained.

Organic Chemistry, Chapter 28, Problem 28.22P , additional homework tip  1Organic Chemistry, Chapter 28, Problem 28.22P , additional homework tip  2

Concept introduction:

Generally, [3, 3] sigmatropic reactions of 1, 5-diences are called as cope reactions. When the diene is having the oxygen at C3 or C4 position the sigmatropic reaction is called as oxy cope reaction. Notably, when the alkoxide fragment is involved it is referred as anionic oxy cope reaction. Moreover, the enhanced increase in rate of sigmatropic reaction and the decreased in the reaction temperature is observed as compared to parent alcohols.

Interpretation Introduction

(b)

Interpretation:

The structure of the product, including its stereochemistry expected from the anion oxyCope reaction of the following compound is to be given.

Organic Chemistry, Chapter 28, Problem 28.22P , additional homework tip  3

Concept introduction:

When the diene is having the oxygen at C3 or C4 position the sigmatropic reaction is called as oxy cope reaction. Notably, when the alkoxide fragment is involved it is referred as anionic oxy cope reaction.

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